Polyhemiaminal and polyhexahydrotriazine materials from 1,4 conjugate addition reactions

Patent metadata

Field	Value
Publication number	US-9458299-B1
Application number	US-201514885706-A
Country	US
Kind code	B1
Filing date	Oct 16, 2015
Priority date	Mar 10, 2015
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

Polyhemiaminal (PHA) and polyhexahydrotriazine (PHT) materials are modified by 1,4 conjugate addition chemical reactions to produce a variety of molecular architectures comprising pendant groups and bridging segments. The materials are formed by a method that includes heating a mixture comprising solvent(s), paraformaldehyde, aromatic amine groups, aliphatic amine Michael donors, and Michael acceptors, such as acrylates. The reaction mixtures may be used to prepare polymer pre-impregnated materials and composites containing PHT matrix resin.

First claim

The invention claimed is:

1. A method of producing a composite article, comprising:
forming a mixture comprising a solvent, paraformaldehyde, an aromatic amine, a Michael addition donor, and a Michael addition acceptor;
heating the mixture to a first temperature to produce a mixture of a first viscosity;
coating a work piece with the mixture of the first viscosity to produce a prepreg;
heating the prepreg to a second temperature to produce a B-stage prepreg of a second viscosity;
cooling the B-stage prepreg;
forming an article from the B-stage prepreg; and
heating the article at a temperature from about 150° C. to about 280° C. to form a cured composite containing polyhexahydrotriazine.

2. The method of claim 1 , wherein the mixture of the first viscosity is produced at a temperature from about 20° C. to about 40° C.

3. The method of claim 1 , wherein the mixture of the first viscosity comprises covalently bonded Michael addition reaction products.

4. The method of claim 1 , wherein the mixture of the first viscosity comprises covalently bonded Michael addition reaction products and PHA oligomers or polymers.

5. The method of claim 2 , wherein the second temperature is about 40° C. to about 145° C.

6. The method of claim 5 , wherein the B-stage prepreg of the second viscosity comprises covalently bonded Michael addition reaction products and PHA oligomers or polymers.

7. The method of claim 1 , wherein the composite article comprises at least an interpenetrating polymer network comprising two or more polymers.

Assignees

• IBM

Inventors

• Boday Dylan J
• Fevre Mareva
• Garcia Jeannette M
• Hedrick James L
• Wojtecki Rudy J

Classifications

• C08G73/0273 Primary

  Polyamines containing heterocyclic moieties in the main chain · CPC title

• C09D5/03

  Powdery paints · CPC title

• C08G73/0644 Primary

  Poly(1,3,5)triazines · CPC title

• C09D161/22

  of aldehydes with acyclic or carbocyclic compounds · CPC title

• C08J5/24 Primary

  Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs · CPC title